Chapter 1: The Warm-Up
Oscar had long since got over his insecurities when it came to being the "token gay guy" at the girls sleepovers.
In fact, tonight was so ridiculously low stakes compared to some of the other things he'd done with this group that his cock was twitching before the first drop of wine even entered his system.
But as the three of them sat sprawled across the futon—Kelly with her legs tucked beneath her, Lola lazily rolling a joint between her fingers, April pressed close enough that he could feel her thigh against his—Oscar's fingers fidgeted with the hem of his t-shirt, his mind racing ahead to what they'd already jokingly planned.
"Alright, loser," Lola said, suddenly tossing the joint aside and rolling to kneel in front of him, her dark eyes glinting.
"Time to put up or shut up, pretty boy. You still in?"
Oscar swallowed hard, his fingers still twiddling with his shirt. "I—yeah. I mean, I said I was, didn’t I?"
April let out a soft giggle, nudging him lightly. "You’re cute when you’re nervous. But we all know you’ve been thinking about this for weeks."
Kelly, ever the voice of reason, reached over and flicked April’s ponytail playfully. "Let the boy breathe, April. He doesn’t need us rushing him." Then, softer, to Oscar: "We’re not pressuring you.
But if you want to stop at any point, just say the word. Got it?"
Oscar nodded, his heart hammering in his chest. He took a deep breath, the smell of patchouli and old wine wrapping around him like a comforting blanket. The fairy lights above them flickered, casting dancing shadows on the walls, and he found himself relaxing into the moment.
Lola leaned in, her sharp green eyes locked onto his, a smirk playing on her lips. "You’re overthinking again," she said, her voice a low purr. "Just relax and let us take care of you."
Before he could respond, Kelly reached out, her fingers brushing against his knee in a reassuring gesture.
"Trust us, Oscar. We’ve got you."
Oscar exhaled slowly, the warmth of her touch lingering on his skin. He nodded again, his fingers finally stilling on his shirt. "Okay. Yeah. I trust you."
Lola grinned, the mischief in her eyes unmistakable. She reached into the duffel bag beside her and pulled out a black harness, the silicone cock already attached, standing firm and glistening under the fairy lights. Oscar’s breath hitched as he watched her slide the harness over her hips, the way the straps hugged her curves.
Kelly’s voice was soft but firm.
“Kneel for her, Oscar.”
He obeyed, his pulse thrumming in his throat as he lowered himself to rest on his heels in front of Lola. The basement floor was cool beneath his knees, and the rough denim of her jeans brushed against his wrists when he rested his hands on her thighs.
Lola didn’t waste a second. She guided him forward with a firm hand on the back of his neck, her grip possessive and gentle at once. “Eyes up,” she murmured, and Oscar lifted his gaze to meet hers.
She was close enough that he could feel the heat from her body, smell the faint trace of vanilla and smoke on her skin.
The silicone cock pressed against his stomach, a blunt pressure that sent a shiver down his spine.
“Relax,” Lola purred, her thumb brushing just beneath his jaw. “Let me in.”
Oscar exhaled shakily, and when she guided him forward, he didn’t resist—only let his lips part slightly as she pressed against him. The first touch was cold, the lube already chilled where it slicked her, but it warmed quickly against his skin. Then she was pushing, and the stretch burned in the best possible way, a deep, aching fullness that made his fingers curl against Lola’s thighs.
“Fuck,” he gasped, his voice rough.
“Fuck, Lola, that’s—”
“That’s what, Oscar?” she teased, her voice a low growl as she pushed deeper, her hips rolling in a slow, steady rhythm. “Tell me what it is.”
Oscar’s breath came in short, sharp gasps, his fingers digging into her thighs as he tried to find the words. “It’s—it’s fucking huge,” he managed, his cheeks flushing. “It’s filling me up, fuck, it’s so good.”
Kelly’s soft laughter filled the room, and Oscar could feel her eyes on him, watching, encouraging. “You look so fucking hot like that, Oscar,” she said, her voice a low purr.
“All flushed and breathless, just for me.” Her fingers tightened in his hair, pulling him back just enough to make him gasp. “You’re taking it so well, aren’t you?” she whispered, her breath hot against his ear. “Good boy.”
Oscar’s cock twitched against his leg.
He was hard, aching, and he couldn’t remember the last time he’d felt this turned on. He rocked back against Lola, his body greedy for more, his breath coming in ragged gasps.
“Fuck, you feel so good,” Lola groaned, her hips snapping forward. “Your ass is so fucking tight, Oscar. I could fuck you all night.”
April, who had been watching quietly, leaned in, her soft voice a contrast to Lola’s rough growls. “Do you like it, Oscar? Do you like having Lola’s big cock in your ass?”
Oscar nodded, his eyes fluttering closed for a moment. “Yeah,” he gasped. “Fuck, yeah.
*Fuck*,” Oscar groaned, his fingers clawing at Lola’s thighs as she thrust forward again, the silicone cock filling him deeper, stretching him open in a way that made his vision blur. “It’s—it’s too much, I can’t—*fuck*—”
Kelly’s hand slid down his back, her nails scraping lightly along his spine before she gripped his ass cheek, pulling him back onto Lola’s cock with a sharp, possessive tug. “That’s it, Oscar,” she murmured, her voice thick with approval. “Take it all. Let her *fuck* you.”
April’s breath hitched as she watched, her fingers tracing lazy circles on Oscar’s shoulder.
“You look so fucking hot like that, Oscar,” she whispered, her voice barely audible over the sound of Lola’s hips slapping against his ass. “I wish I could feel what you’re feeling. I wish I could feel how full you are, how good it feels to have something so big inside you.”
Oscar’s eyes fluttered open, meeting April’s gaze, and he let out a ragged moan. “Fuck, April, it feels—it feels so fucking good. I can’t—” He broke off with a gasp as Lola shifted her angle, her cock hitting that spot inside him that made his toes curl.
“Fuck, fuck, *fuck*—” His voice cracked, his fingers digging into Lola’s thighs so hard his knuckles turned white. “I can’t—I can’t take it, I’m gonna—”
Kelly’s fingers tangled in his hair, yanking his head back just enough to make his neck arch. “You’re gonna what, Oscar?” she demanded, her voice a dark, velvety purr. “You’re gonna come? You’re gonna beg? You’re gonna let us *ruin* you?”
Oscar whimpered, his body trembling on the verge of something he couldn’t even name yet. “I—I don’t know,” he admitted, his voice raw.
His hips bucked instinctively, chasing the pleasure that was threatening to overwhelm him. “I just—I can’t think straight when you’re doing that.”
Lola’s laugh was a dark, throaty sound, her hips rolling in a way that made the silicone cock inside him pulse and stretch. “Good,” she murmured, her fingers tangling in his hair, yanking his head back just enough to expose his throat. “Because you’re ours now, Oscar. And you’re gonna take whatever we give you.”
Kelly’s breath was hot against his ear as she spoke, her voice a low, sinister whisper. “You’re gonna come for us, aren’t you?
You’re gonna come all over yourself while Lola fucks you senseless,” Kelly whispered, her tongue tracing the shell of his ear. Oscar shivered, his cock throbbing at the filthy words. He could feel the heat building in his belly, the pressure coiling tight at the base of his spine.
“Fuck, yes,” he gasped, his hips bucking forward, chasing the friction he needed. “I’m gonna come, I’m gonna fucking come—”
Lola’s grip on his hair tightened, her hips slapping against his ass in a punishing rhythm. “Not yet, you’re not,” she growled, her voice a dark command.
“Not until we say so. You’re gonna hold it back, Oscar. You’re gonna hold it back until we tell you to let go.”
Oscar’s eyes fluttered closed, his body trembling with the effort of holding back his orgasm. He could feel the pressure building, the heat in his belly coiling tighter and tighter, like a spring ready to snap. His cock throbbed, leaking precome onto his thigh, and he let out a ragged moan, his fingers clawing at Lola’s thighs.
“Fuck, Lola, please,” he gasped, his voice a desperate plea.
“I can’t—I can’t hold it back much longer.”
Kelly’s hand slid down his chest, her fingers tracing the lines of his abs before she wrapped her hand around his cock, her grip tight and unyielding. “You can,” she murmured, her voice a dark promise. “And you will. Because you want to please us, don’t you, Oscar?”
Oscar nodded, his eyes fluttering closed as Kelly began to stroke him in slow, steady movements, her thumb brushing over the head of his cock, spreading the precome that leaked from the tip.
His breath came in sharp, ragged gasps as she worked him, her grip firm and unyielding, her touch sending waves of pleasure through his body.
“Fuck, Kelly,” he groaned, his fingers digging into Lola’s thighs. “That feels—*fuck*—that feels so good.”
Lola’s laugh was a dark, throaty sound, her hips rolling in a way that made the silicone cock inside him pulse and stretch. “Good?” she taunted, her voice a low growl. “You’re not even close, baby.
You feel fucking incredible,” Lola purred, her hips snapping forward, driving the silicone cock deeper into Oscar. “I could fuck you all night, feel that tight little ass gripping me, begging for more.”
Kelly’s hand on Oscar’s cock sped up, her grip tightening as she worked him in time with Lola’s thrusts. “Come on, Oscar,” she whispered, her voice a dark, velvety purr. “Show us how much you love it. Show us how close you are.”
Oscar’s breath hitched, his body trembling as he fought to hold back his orgasm. “Fuck, Kelly, I—I can’t,” he gasped, his fingers clawing at Lola’s thighs.
“I can’t hold back much longer.”
April’s soft voice cut through the haze of pleasure, her fingers brushing against his cheek. “It’s okay, Oscar. You can do it. You’re doing so well.”
Oscar’s eyes fluttered open, meeting April’s gaze, and he found the strength to nod, to hold back the orgasm that was threatening to consume him. “Yeah, I can do this. I can hold back.”
Lola’s grin was wicked, her hips snapping forward in a punishing rhythm. “That’s right, baby. You’re doing so good.
Such a good fucking boy for us, aren’t you?” Lola’s voice was a rough, rasping growl, her hips slamming into Oscar’s ass with enough force to make his teeth clack together. The silicone cock inside him pulsed, stretching him open in a way that made his vision blur. “You’re taking it like a fucking champ, Oscar. You’re gonna come so hard for us, aren’t you?”
Oscar’s breath came in sharp, ragged gasps as he fought to hold back his orgasm. His fingers dug into Lola’s thighs, his knuckles turning white as he tried to find something to anchor himself to.
The pleasure was overwhelming, a tidal wave threatening to drown him, and he needed something—anything—to keep him grounded.
Kelly’s hand on his cock was relentless, her grip tight and unyielding as she worked him in time with Lola’s thrusts. Her thumb brushed over the head of his cock, spreading the precome that leaked from the tip, and Oscar let out a ragged moan, his hips bucking forward instinctively.
“Fuck, Kelly, please,” he gasped, his voice a desperate plea. “I can’t—I can’t hold back much longer.”
Lola’s laugh was a dark, throaty sound, her hips slapping against his ass in a punishing rhythm.
You feel fucking incredible. I could fuck you all night, feel that tight little ass gripping me, begging for more.”
Kelly’s hand on Oscar’s cock sped up, her grip tightening as she worked him in time with Lola’s thrusts.
The silicone cock inside Oscar pulsed and stretched him open, the pressure building to a point where he could feel it in his bones. His fingers dug into Lola’s thighs, his knuckles turning white as he fought to hold back the orgasm that threatened to consume him.
“Fuck, Lola, I can’t—I’m gonna—” Oscar’s voice cracked, his breath coming in short, sharp gasps.
Kelly’s voice was a low, sinister whisper, her breath hot against his ear. “You can cum now" she murmured, her fingers tightening around his cock. “But only if you beg for it.”
Oscar’s breath hitched, his body trembling with the effort of holding back. He was so close, so fucking close, but the thought of coming without permission—of disobeying them—made his cock jerk in Kelly’s grip. “Please,” he gasped, his voice raw. “I—I can’t hold back anymore.”
Lola’s laugh was a dark, throaty sound, her hips slamming into him with enough force to make his teeth clack together. “That’s the spirit,” she growled, her fingers tangling in his hair, yanking his head back just enough to expose his throat.
“Beg for it, Oscar. Beg us to let you come.”
Oscar’s lips parted on a whimper, his body trembling with the effort of holding back. His cock throbbed in Kelly’s grip, leaking precome in thick, desperate spurts.
“Please,” he gasped, his voice breaking. “I need to come.
Fuck, I need to come so bad,” Oscar panted, his voice ragged with desperation. His hips bucked forward, chasing the friction he needed, but Lola’s grip on his hair held him in place, her hips slapping against his ass in a punishing rhythm.
“Not yet, baby,” Lola growled, her voice a dark command. “You’re gonna come when we say so. And not a second before.”
Kelly’s hand on his cock slowed, her grip tightening as she worked him in slow, torturous strokes. “You’re gonna beg for it, Oscar,” she murmured, her voice a low, velvety purr.
“Beg us to let you come. Beg us to ruin you.”
Oscar’s breath hitched, his body trembling in Lola’s grip. His cock throbbed in Kelly’s hand, leaking precome in thick, desperate spurts. “I need to come, Lola. I need to fucking come so bad.”
Lola’s laugh was a dark, throaty sound, her hips slamming into him with enough force to make his teeth clack together.
“That’s the spirit, Oscar,” she growled, her fingers digging into his hair, yanking his head back just enough to expose his throat. “You’re gonna beg for it, aren’t you?”
Oscar’s breath hitched, his body trembling in Lola’s grip. He could feel the pressure building inside him, like a coiled spring ready to snap, and his hips bucked instinctively against the silicone cock inside him.
He was so fucking close, so fucking desperate, and he couldn't hold back much longer.
"Please," he gasped, his voice ragged with desperation. "I need to come. Fuck, I need to come so bad."
Lola's grip on his hair tightened, her hips slapping against his ass in a punishing rhythm. "Not yet, baby," she growled, her voice a dark command. "You're gonna come when we say so. And not a second before."
Kelly's hand on his cock slowed, her grip tightening as she worked him in slow, torturous strokes.
"ten....nine...." She began the countdown , her voice a low, sultry purr. "Eight...seven...six...five...four...three...two...one."
Oscar's breath hitched, his body tensing as he waited for the command. He could feel the pressure building inside him, the heat in his belly coiling tighter and tighter, like a spring ready to snap. His cock throbbed in Kelly's grip, leaking precome in thick, desperate spurts.
"Now, Oscar," Kelly whispered, her voice a dark, velvety command. "Come for us."
Oscar's body convulsed, his orgasm ripping through him with the force of a hurricane.
He let out a ragged, desperate cry, his fingers clawing at Lola's thighs as he came undone, his cock pulsing in Kelly's grip as he spilled over her hand, his release coating her fingers in thick, hot ropes of come.
"Fuck, fuck, *fuck*!" he gasped, his body trembling as he rode out the waves of pleasure that crashed over him. "I'm coming, I'm fucking coming so hard—"
Lola's grip on his hair tightened, her hips slapping against his ass as she fucked him through his orgasm, her cock pulsing inside him, filling him with the silicone's heat.
Kelly's hand on his cock tightened as well, milking his release, her thumb swirling over the sensitive head as he came, his cum painting her fingers in thick, hot ropes.
"Fuck, fuck, *fuck*—" Oscar gasped, his voice breaking as the pleasure overwhelmed him. His body jerked, his cock pulsing in Kelly's grip as he spilled over her hand, his release coating her fingers in thick, hot ropes.
Kelly's eyes darkened, her gaze locked onto Oscar as she watched him come undone. "Good boy," she murmured, her voice thick with approval.